


Cross Dressing Steve (Headcanon)

by look_turtles



Series: Steve/Billy Headcanons [3]
Category: Stranger Things (TV 2016)
Genre: F/M, M/M
Language: English
Status: Completed
Published: 2018-06-24
Updated: 2018-06-24
Packaged: 2019-05-27 19:19:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 454
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15031496
Author URL: https://archiveofourown.org/users/look_turtles/pseuds/look_turtles
Summary: It all started with a bet





	Cross Dressing Steve (Headcanon)

The first time Steve tried on women's underwear, he and Nancy were in his room. They were drunk from the liquor from his dad liquor cabinet. As Nancy laughed, she dared Steve to try on her pink silk underwear.

Never one to back down from a challenge, King Steve put them on. As the soft fabric slid over his balls he felt himself harden.

For days afterward, all he could think about were those underwear and how good they felt.

He decided to do something and went two towns over (it wouldn't do for King Steve to get caught) and walked into a lingerie shop and stared at all the underwear and bras.

He picked out a pair of red silk panties and nervously made his way to the counter. As the bored looking saleswoman rang up his purchase, he made sure to say that they were for his girlfriend even though no one asked.

He couldn't get home fast enough and as soon as he was safely in his room with the door locked, he pulled off his pants and put on his new underwear. He groaned as the soft fabric slid over his skin. He ended up jerking off with the panties slid down just below his balls.

Years later, his collection of panties has grown so big that they were piled into a big cardboard box hidden under his bed.

It isn't just the feeling of the fabric that is a turn on, but the fact that it's something forbidden.

One day Steve was in his room wearing a pair of black lacey panties and was so enamored with them that he doesn’t hear Billy’s car pull up. He doesn’t hear the front door open and close, but he does hear when Billy opened the bedroom door and he really heard Billy’s gasp when he saw Steve.

‘What the hell?! Billy exclaimed as he walked over to where Steve was laying on his bed in parties for the whole world to see. 

They might not be enemies anymore, but he wouldn’t put it past Billy to tell the whole school about the underwear.

‘Um... this isn’t what it looks like,’ Steve said trying and failing to cover himself.

Billy gently ran his hand over Steve’s leg and underwear. ‘Really because it looks like you’re hot.’

Steve eyes went wide. ‘Really?!

Billy winked. ‘Oh, Yeah. Why don’t you show me just how hot you are.’

That night Billy sucked Steve off while Steve has his panties around his thighs. 

Steve wanted to show Billy his collection of underwear (and have lots of sex) but there will be time for that later.

* * *

If anyone wants to use this Headcanon for fanworks feel free.


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